CA2387134C - Cyclopropanes as cgrp antagonists, medicaments containing said compounds and method for the production thereof - Google Patents

Cyclopropanes as cgrp antagonists, medicaments containing said compounds and method for the production thereof Download PDF

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Publication number: CA2387134C
Authority: CA; Canada
Prior art keywords: amino; salt; tautomer; enantiomer; groups
Prior art date: 1999-10-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002387134A

Other languages

English (en)

French (fr)

Other versions

CA2387134A1 (en

Inventor

Wolfgang Eberlein

Wolfhard Engel

Klaus Rudolf

Henri Doods

Gerhard Hallermayer

Eckhart Bauer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Boehringer Ingelheim Pharma GmbH and Co KG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-10-29

Filing date

2000-10-21

Publication date

2008-07-08

2000-10-21 Application filed by Boehringer Ingelheim Pharma GmbH and Co KG filed Critical Boehringer Ingelheim Pharma GmbH and Co KG

2001-05-10 Publication of CA2387134A1 publication Critical patent/CA2387134A1/en

2008-07-08 Application granted granted Critical

2008-07-08 Publication of CA2387134C publication Critical patent/CA2387134C/en

2020-10-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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150000001875 compounds Chemical class 0.000 title claims abstract description 72
238000000034 method Methods 0.000 title claims abstract description 26
238000004519 manufacturing process Methods 0.000 title claims description 5
150000001942 cyclopropanes Chemical class 0.000 title description 4
229940127597 CGRP antagonist Drugs 0.000 title description 3
239000003814 drug Substances 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 82
239000000203 mixture Substances 0.000 claims abstract description 60
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 9
230000008569 process Effects 0.000 claims abstract description 9
150000007522 mineralic acids Chemical class 0.000 claims abstract description 6
150000007524 organic acids Chemical class 0.000 claims abstract description 6
-1 biphenylyl Chemical group 0.000 claims description 158
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
125000000623 heterocyclic group Chemical group 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 29
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 28
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 28
125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 21
229910052799 carbon Inorganic materials 0.000 claims description 20
239000000460 chlorine Substances 0.000 claims description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
229910052801 chlorine Inorganic materials 0.000 claims description 18
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 18
125000001246 bromo group Chemical group Br* 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 16
229910052731 fluorine Inorganic materials 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
229910021529 ammonia Inorganic materials 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 8
125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 8
125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000003226 pyrazolyl group Chemical group 0.000 claims description 8
125000000168 pyrrolyl group Chemical group 0.000 claims description 8
238000007127 saponification reaction Methods 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
206010047141 Vasodilatation Diseases 0.000 claims description 6
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000002837 carbocyclic group Chemical group 0.000 claims description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
208000027866 inflammatory disease Diseases 0.000 claims description 6
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
238000006467 substitution reaction Methods 0.000 claims description 6
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
230000024883 vasodilation Effects 0.000 claims description 6
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
208000024172 Cardiovascular disease Diseases 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
206010019233 Headaches Diseases 0.000 claims description 5
206010027304 Menopausal symptoms Diseases 0.000 claims description 5
206010039085 Rhinitis allergic Diseases 0.000 claims description 5
230000001154 acute effect Effects 0.000 claims description 5
201000010105 allergic rhinitis Diseases 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
230000017531 blood circulation Effects 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
231100000869 headache Toxicity 0.000 claims description 5
229960005181 morphine Drugs 0.000 claims description 5
238000011321 prophylaxis Methods 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
208000017520 skin disease Diseases 0.000 claims description 5
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 4
WRIOMYHORIZPQI-QZTJIDSGSA-N 2-[[3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-2-oxo-1,4-dihydroquinazolin-6-yl]oxy]acetic acid Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(OCC(O)=O)C=C3C2)=O)C1 WRIOMYHORIZPQI-QZTJIDSGSA-N 0.000 claims description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
VCCFJGGMPHWKAG-QZTJIDSGSA-N 2-[[3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-2-oxo-1,4-dihydroquinazoline-7-carbonyl]amino]acetic acid Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC(=CC=C3C2)C(=O)NCC(O)=O)=O)C1 VCCFJGGMPHWKAG-QZTJIDSGSA-N 0.000 claims description 3
AZJCEKSGDAMLRT-IAGOWNOFSA-N 3-[1-[(1r,2r)-2-(3,5-dibromo-4-hydroxybenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=CC=C3C2)=O)C1 AZJCEKSGDAMLRT-IAGOWNOFSA-N 0.000 claims description 3
TYFPBOVUBMAMRQ-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(3,5-dibromo-4-hydroxybenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-phenyl-1h-imidazol-2-one Chemical compound C1=C(Br)C(O)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=CC=CC=2)=O)C1 TYFPBOVUBMAMRQ-QZTJIDSGSA-N 0.000 claims description 3
JPQLSUWZCNNNRO-HZPDHXFCSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-1,4-dihydropyrido[4,3-d]pyrimidin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=NC=C3C2)=O)C1 JPQLSUWZCNNNRO-HZPDHXFCSA-N 0.000 claims description 3
KUKIMOYIGBFOHW-IAGOWNOFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=CC=C3C2)=O)C1 KUKIMOYIGBFOHW-IAGOWNOFSA-N 0.000 claims description 3
KGCTUCGSJISGTH-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(2-methoxyphenyl)-1h-imidazol-2-one Chemical compound COC1=CC=CC=C1C(NC1=O)=CN1C1CCN(C(=O)[C@H]2[C@@H](C2)C(=O)C=2C=C(Br)C(N)=C(Br)C=2)CC1 KGCTUCGSJISGTH-QZTJIDSGSA-N 0.000 claims description 3
NUWMYMFUHBRBHR-HZPDHXFCSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(3,4-dichlorophenyl)-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=C(Cl)C(Cl)=CC=2)=O)C1 NUWMYMFUHBRBHR-HZPDHXFCSA-N 0.000 claims description 3
JYOGPDQDXPDNHR-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(3-chlorophenyl)-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=C(Cl)C=CC=2)=O)C1 JYOGPDQDXPDNHR-QZTJIDSGSA-N 0.000 claims description 3
NUBNSKOIGYPWDD-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(3-hydroxyphenyl)-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=C(O)C=CC=2)=O)C1 NUBNSKOIGYPWDD-QZTJIDSGSA-N 0.000 claims description 3
HHDCMJIIDLWDMD-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-(3-nitrophenyl)-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=C(C=CC=2)[N+]([O-])=O)=O)C1 HHDCMJIIDLWDMD-QZTJIDSGSA-N 0.000 claims description 3
CGGOFRMDQCXLKQ-IAGOWNOFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-[2-(trifluoromethyl)phenyl]-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C(=CC=CC=2)C(F)(F)F)=O)C1 CGGOFRMDQCXLKQ-IAGOWNOFSA-N 0.000 claims description 3
RLJLQNLYLWGOES-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-5-phenyl-1h-imidazol-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC(=C2)C=2C=CC=CC=2)=O)C1 RLJLQNLYLWGOES-QZTJIDSGSA-N 0.000 claims description 3
UTATXYLZLKRHCP-WOJBJXKFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-(1,3-dioxolan-2-ylmethoxy)-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(OCC4OCCO4)C=C3C2)=O)C1 UTATXYLZLKRHCP-WOJBJXKFSA-N 0.000 claims description 3
GMDCYGYKWYIQLG-DHIUTWEWSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-(2-morpholin-4-ylethoxy)-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(OCCN4CCOCC4)C=C3C2)=O)C1 GMDCYGYKWYIQLG-DHIUTWEWSA-N 0.000 claims description 3
FZWCJVAIYGDWGT-FGZHOGPDSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-(4-methylpiperazin-1-yl)-1,4-dihydroquinazolin-2-one Chemical compound C1CN(C)CCN1C1=CC=C(NC(=O)N(C2)C3CCN(CC3)C(=O)[C@H]3[C@@H](C3)C(=O)C=3C=C(Br)C(N)=C(Br)C=3)C2=C1 FZWCJVAIYGDWGT-FGZHOGPDSA-N 0.000 claims description 3
TYNFKVRBQZCNFK-NHCUHLMSSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-[2-(dimethylamino)ethoxy]-1,4-dihydroquinazolin-2-one Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1C(=O)NC2=CC=C(C=C2C1)OCCN(C)C)C1=CC(Br)=C(N)C(Br)=C1 TYNFKVRBQZCNFK-NHCUHLMSSA-N 0.000 claims description 3
FVBTUAQLPAVBGJ-FGZHOGPDSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-[3-(dimethylamino)propoxy]-1,4-dihydroquinazolin-2-one Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1C(=O)NC2=CC=C(C=C2C1)OCCCN(C)C)C1=CC(Br)=C(N)C(Br)=C1 FVBTUAQLPAVBGJ-FGZHOGPDSA-N 0.000 claims description 3
RJUWQQNNJRIGJM-IAGOWNOFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-bromo-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(Br)C=C3C2)=O)C1 RJUWQQNNJRIGJM-IAGOWNOFSA-N 0.000 claims description 3
QJILSEPJTKVBDW-IAGOWNOFSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-6-hydroxy-1,4-dihydroquinazolin-2-one Chemical compound C1=C(Br)C(N)=C(Br)C=C1C(=O)[C@H]1[C@H](C(=O)N2CCC(CC2)N2C(NC3=CC=C(O)C=C3C2)=O)C1 QJILSEPJTKVBDW-IAGOWNOFSA-N 0.000 claims description 3
URTGWCFRADYXNO-QZTJIDSGSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-7-methoxy-1,4-dihydroquinazolin-2-one Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1CC2=CC=C(C=C2NC1=O)OC)C1=CC(Br)=C(N)C(Br)=C1 URTGWCFRADYXNO-QZTJIDSGSA-N 0.000 claims description 3
SEKOHRSMEOMYFS-NHCUHLMSSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-n,n-diethyl-2-oxo-1,4-dihydroquinazoline-7-carboxamide Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1CC2=CC=C(C=C2NC1=O)C(=O)N(CC)CC)C1=CC(Br)=C(N)C(Br)=C1 SEKOHRSMEOMYFS-NHCUHLMSSA-N 0.000 claims description 3
ZQBVLOYAQVSSQR-FGZHOGPDSA-N 3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-n-[2-(dimethylamino)ethyl]-n-methyl-2-oxo-1,4-dihydroquinazoline-7-carboxamide Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1CC2=CC=C(C=C2NC1=O)C(=O)N(C)CCN(C)C)C1=CC(Br)=C(N)C(Br)=C1 ZQBVLOYAQVSSQR-FGZHOGPDSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
HVPPCCNZJYCCGV-RTBURBONSA-N methyl 2-[[3-[1-[(1r,2r)-2-(4-amino-3,5-dibromobenzoyl)cyclopropanecarbonyl]piperidin-4-yl]-2-oxo-1,4-dihydroquinazolin-7-yl]oxy]acetate Chemical compound O=C([C@@H]1C[C@H]1C(=O)N1CCC(CC1)N1CC2=CC=C(C=C2NC1=O)OCC(=O)OC)C1=CC(Br)=C(N)C(Br)=C1 HVPPCCNZJYCCGV-RTBURBONSA-N 0.000 claims description 3
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150000003335 secondary amines Chemical class 0.000 description 1
230000035939 shock Effects 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
230000037380 skin damage Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229940086766 sodium chloride 180 mg Drugs 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000000758 substrate Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
RVLBWBWZOLQRMM-UHFFFAOYSA-N tert-butyl 4-(6-bromo-2-oxo-1,4-dihydroquinazolin-3-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C(=O)NC2=CC=C(Br)C=C2C1 RVLBWBWZOLQRMM-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
238000005533 tritiation Methods 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
229940102566 valproate Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
WEKISHNHYNINFX-UHFFFAOYSA-N zinc;iodomethane Chemical compound [Zn+2].I[CH2-].I[CH2-] WEKISHNHYNINFX-UHFFFAOYSA-N 0.000 description 1
ULSDMUVEXKOYBU-ZDUSSCGKSA-N zolmitriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1C[C@H]1COC(=O)N1 ULSDMUVEXKOYBU-ZDUSSCGKSA-N 0.000 description 1
229960001360 zolmitriptan Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Dermatology (AREA)
Emergency Medicine (AREA)
Otolaryngology (AREA)
Hematology (AREA)
Obesity (AREA)
Immunology (AREA)
Toxicology (AREA)
Rheumatology (AREA)
Heart & Thoracic Surgery (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

CA002387134A 1999-10-29 2000-10-21 Cyclopropanes as cgrp antagonists, medicaments containing said compounds and method for the production thereof Expired - Fee Related CA2387134C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19952147A DE19952147A1 (de)	1999-10-29	1999-10-29	Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE19952147.6		1999-10-29
PCT/EP2000/010391 WO2001032648A1 (de)	1999-10-29	2000-10-21	Neue cyclopropane als cgrp-antagonisten, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (2)

Publication Number	Publication Date
CA2387134A1 CA2387134A1 (en)	2001-05-10
CA2387134C true CA2387134C (en)	2008-07-08

Family

ID=7927315

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002387134A Expired - Fee Related CA2387134C (en)	1999-10-29	2000-10-21	Cyclopropanes as cgrp antagonists, medicaments containing said compounds and method for the production thereof

Country Status (26)

Country	Link
US (2)	US20030139417A1 (cs)
EP (1)	EP1228059B1 (cs)
JP (1)	JP3869721B2 (cs)
KR (1)	KR20020047290A (cs)
CN (1)	CN1177844C (cs)
AT (1)	ATE301117T1 (cs)
AU (1)	AU781856B2 (cs)
BG (1)	BG106638A (cs)
BR (1)	BR0015147A (cs)
CA (1)	CA2387134C (cs)
CZ (1)	CZ20021812A3 (cs)
DE (2)	DE19952147A1 (cs)
EA (1)	EA005137B1 (cs)
EE (1)	EE200200220A (cs)
HR (1)	HRP20020373A2 (cs)
HU (1)	HUP0203496A3 (cs)
IL (1)	IL148975A0 (cs)
MX (1)	MXPA02004119A (cs)
NO (1)	NO20021799L (cs)
NZ (1)	NZ518698A (cs)
PL (1)	PL354715A1 (cs)
SK (1)	SK7282002A3 (cs)
TR (1)	TR200201168T2 (cs)
WO (1)	WO2001032648A1 (cs)
YU (1)	YU30902A (cs)
ZA (1)	ZA200203256B (cs)

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US7842808B2 (en)	2002-06-05	2010-11-30	Bristol-Myers Squibb Company	Anti-migraine spirocycles
ES2616539T3 (es) *	2002-06-05	2017-06-13	Bristol-Myers Squibb Company	Antagonistas de receptores de péptidos relacionados con el gen de calcitonina
US7220862B2 (en)	2002-06-05	2007-05-22	Bristol-Myers Squibb Company	Calcitonin gene related peptide receptor antagonists
JP2007524568A (ja)	2003-12-05	2007-08-30	ブリストル−マイヤーズ　スクイブ　カンパニー	カルシトニン遺伝子関連ペプチドレセプターアンタゴニスト
TW200524601A (en)	2003-12-05	2005-08-01	Bristol Myers Squibb Co	Heterocyclic anti-migraine agents
TW200533398A (en)	2004-03-29	2005-10-16	Bristol Myers Squibb Co	Novel therapeutic agents for the treatment of migraine
JP2008512459A (ja) *	2004-09-09	2008-04-24	メルクエンドカムパニーインコーポレーテッド	アリールスピロラクタムｃｇｒｐ受容体拮抗薬
US7384931B2 (en)	2004-11-03	2008-06-10	Bristol-Myers Squibb Company	Constrained compounds as CGRP-receptor antagonists
US7384930B2 (en)	2004-11-03	2008-06-10	Bristol-Myers Squibb Company	Constrained compounds as CGRP-receptor antagonists
US7449586B2 (en)	2004-12-03	2008-11-11	Bristol-Myers Squibb Company	Processes for the preparation of CGRP-receptor antagonists and intermediates thereof
US7834007B2 (en)	2005-08-25	2010-11-16	Bristol-Myers Squibb Company	CGRP antagonists
EP1954135B1 (en) *	2005-11-18	2012-10-10	Merck Sharp & Dohme Corp.	Spirolactam aryl cgrp receptor antagonists
WO2009034029A2 (de) *	2007-09-07	2009-03-19	Boehringer Ingelheim International Gmbh	1-substituierte 4 -heterocyclylpiperidine als cgrp antagonisten
NZ585347A (en)	2007-10-18	2011-09-30	Boehringer Ingelheim Int	Cgrp antagonists
EP2065381A1 (de)	2007-10-18	2009-06-03	Boehringer Ingelheim Pharma GmbH & Co. KG	CGRP Antagonisten
EP2225223B1 (de)	2007-11-22	2017-01-11	Boehringer Ingelheim International GmbH	Organische verbindungen
US9315449B2 (en)	2008-05-15	2016-04-19	Duke University	Substituted pyrazoles as heat shock transcription factor activators
UA105182C2 (ru)	2008-07-03	2014-04-25	Ньюрексон, Інк.	Бензоксазины, бензотиазины и родственные соединения, которые имеют ингибирующую nos активность
JP6275690B2 (ja)	2012-04-05	2018-02-07	シーエイチディーアイファウンデーション，インコーポレーテッド	キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法
JP6449893B2 (ja)	2013-09-26	2019-01-09	シーエイチディーアイファウンデーション，インコーポレーテッド	キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法
JP2016536350A (ja)	2013-09-26	2016-11-24	シーエイチディーアイファウンデーション，インコーポレーテッド	キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法
JP2019040859A (ja) *	2017-08-22	2019-03-14	株式会社エンプラス	発光装置、面光源装置および光束制御部材
CN114957145B (zh) *	2022-04-14	2023-07-18	浙江师范大学	一种1,2,4-苯并三嗪衍生物及其制备方法

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FR2729855A1 (fr)	1995-01-26	1996-08-02	Oreal	Utilisation d'un antagoniste de cgrp dans une composition cosmetique, pharmaceutique ou dermatologique et composition obtenue
JP3048067B2 (ja)	1995-12-15	2000-06-05	ノボノルディスクアクティーゼルスカブ	新規方法
EP0934068A1 (en) *	1996-09-09	1999-08-11	Smithkline Beecham Corporation	Compounds and methods
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JP2002506863A (ja) *	1998-03-17	2002-03-05	ノボノルディスクアクティーゼルスカブ	新規ヘテロ環式化合物
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DE19937304C2 (de)	1999-08-10	2003-08-21	Boehringer Ingelheim Pharma	Verwendung von CGRP-Antagonisten zur Bekämpfung menopausaler Hitzewallungen
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TWI227231B (en) *	2000-07-12	2005-02-01	Novartis Ag	4-benzoyl-piperidine derivatives for treating conditions mediated by CCR-3
AU2002223968A1 (en) *	2000-12-21	2002-07-01	Warner Lambert Company Llc	Piperidine derivatives as subtype selective n-methyl-d-aspartate antagonists
US20030191110A1 (en) *	2001-11-01	2003-10-09	Martyn Botfield	Modulators of the cholesterol biosynthetic pathway
US6977265B2 (en) *	2001-11-30	2005-12-20	Roche Palo Alto Llc	Piperidine CCR-3 receptor antagonists
US7026312B2 (en) *	2002-03-14	2006-04-11	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof

1999
- 1999-10-29 DE DE19952147A patent/DE19952147A1/de not_active Withdrawn
2000
- 2000-10-21 BR BR0015147-5A patent/BR0015147A/pt not_active IP Right Cessation
- 2000-10-21 AT AT00969529T patent/ATE301117T1/de not_active IP Right Cessation
- 2000-10-21 SK SK728-2002A patent/SK7282002A3/sk unknown
- 2000-10-21 NZ NZ518698A patent/NZ518698A/xx unknown
- 2000-10-21 IL IL14897500A patent/IL148975A0/xx unknown
- 2000-10-21 HR HR20020373A patent/HRP20020373A2/hr not_active Application Discontinuation
- 2000-10-21 EP EP00969529A patent/EP1228059B1/de not_active Expired - Lifetime
- 2000-10-21 KR KR1020027005386A patent/KR20020047290A/ko not_active Withdrawn
- 2000-10-21 CZ CZ20021812A patent/CZ20021812A3/cs unknown
- 2000-10-21 CA CA002387134A patent/CA2387134C/en not_active Expired - Fee Related
- 2000-10-21 HU HU0203496A patent/HUP0203496A3/hu unknown
- 2000-10-21 JP JP2001534799A patent/JP3869721B2/ja not_active Expired - Fee Related
- 2000-10-21 CN CNB008151490A patent/CN1177844C/zh not_active Expired - Fee Related
- 2000-10-21 EA EA200200447A patent/EA005137B1/ru not_active IP Right Cessation
- 2000-10-21 AU AU79213/00A patent/AU781856B2/en not_active Ceased
- 2000-10-21 DE DE50010886T patent/DE50010886D1/de not_active Expired - Fee Related
- 2000-10-21 EE EEP200200220A patent/EE200200220A/xx unknown
- 2000-10-21 YU YU30902A patent/YU30902A/sh unknown
- 2000-10-21 WO PCT/EP2000/010391 patent/WO2001032648A1/de not_active Ceased
- 2000-10-21 PL PL00354715A patent/PL354715A1/xx not_active Application Discontinuation
- 2000-10-21 TR TR2002/01168T patent/TR200201168T2/xx unknown
- 2000-10-21 MX MXPA02004119A patent/MXPA02004119A/es unknown
2002
- 2002-04-12 US US10/121,872 patent/US20030139417A1/en not_active Abandoned
- 2002-04-17 NO NO20021799A patent/NO20021799L/no not_active Application Discontinuation
- 2002-04-23 BG BG106638A patent/BG106638A/bg unknown
- 2002-04-24 ZA ZA200203256A patent/ZA200203256B/en unknown
2005
- 2005-06-27 US US11/169,078 patent/US7407963B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
BG106638A (bg)	2003-01-31
ZA200203256B (en)	2003-04-10
HUP0203496A2 (hu)	2003-02-28
PL354715A1 (en)	2004-02-09
WO2001032648A1 (de)	2001-05-10
EP1228059B1 (de)	2005-08-03
CN1177844C (zh)	2004-12-01
EP1228059A1 (de)	2002-08-07
NO20021799D0 (no)	2002-04-17
ATE301117T1 (de)	2005-08-15
DE19952147A1 (de)	2001-05-03
HK1051858A1 (en)	2003-08-22
CZ20021812A3 (cs)	2002-08-14
JP2003513087A (ja)	2003-04-08
US7407963B2 (en)	2008-08-05
NO20021799L (no)	2002-04-17
KR20020047290A (ko)	2002-06-21
SK7282002A3 (en)	2002-11-06
MXPA02004119A (es)	2003-10-06
CN1387526A (zh)	2002-12-25
AU781856B2 (en)	2005-06-16
BR0015147A (pt)	2002-07-16
HUP0203496A3 (en)	2004-01-28
CA2387134A1 (en)	2001-05-10
US20050267137A1 (en)	2005-12-01
YU30902A (sh)	2005-07-19
IL148975A0 (en)	2002-11-10
US20030139417A1 (en)	2003-07-24
EA005137B1 (ru)	2004-12-30
JP3869721B2 (ja)	2007-01-17
NZ518698A (en)	2004-12-24
HRP20020373A2 (en)	2003-10-31
EA200200447A1 (ru)	2002-10-31
AU7921300A (en)	2001-05-14
TR200201168T2 (tr)	2002-08-21
DE50010886D1 (de)	2005-09-08
EE200200220A (et)	2003-06-16

Legal Events

Date	Code	Title	Description
2003-11-19	EEER	Examination request
2010-10-21	MKLA	Lapsed

Publication	Publication Date	Title
AU781856B2 (en)	2005-06-16	Novel cyclopropanes as CGRP antagonists, medicaments containing said compounds and method for the production thereof
US7230001B1 (en)	2007-06-12	Arylalkane, arylalkene and aryl azaalkane, medicaments containing said compounds and method for the production thereof
US7205294B2 (en)	2007-04-17	Selected CGRP-antagonists process for preparing them and their use as pharmaceutical compositions
US8765763B2 (en)	2014-07-01	Substituted piperazines as CGRP antagonists
US6949541B2 (en)	2005-09-27	Substituted piperidines, medicaments containing these compounds, and methods for the production thereof
US20040192729A1 (en)	2004-09-30	Carboxylic acids and the esters thereof, pharmaceutical compositions thereto and processes for the preparation thereof
CA2562529A1 (en)	2005-10-27	Selected cgrp antagonists, methods for the production thereof, and use thereof as medicaments
CA2600909A1 (en)	2006-09-28	Cgrp antagonists, method for the production thereof, and their use as medicaments
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